Ethanol → HCID 15463354, compound

HRID 1636881Notes

Reaction equation

HRID 1636881 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])=[C:5]([CH3:14])[C:6]=1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].N1C=CC=CC=1.[C:31](Cl)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CCO>C(Cl)Cl.O>[C:32]1([C:31]([NH:1][C:2]2[S:3][C:4]([C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[O:16])=[C:5]([CH3:14])[C:6]=2[C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])=[O:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 1049PyridineHCID 7412Benzoyl chlorideHCID 10882569HCID 10882569, compound

Product 1

HCID 15463354HCID 15463354, compoundYield 83.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of the compound prepared in Example 2 (2.78 g, 8.00 mmol), pyridine (1.6 ml, 20 mmol) and DCM (35 ml) was added benzoyl chloride (1.18 g, 8.40 mmol) dropwise. After 18 hours, the reaction was diluted reaction with EtOH and stirred for 1 hour. The reaction solution was diluted with DCM and H2O. The layers were separated and the aqueous layer was extracted with DCM. The combined aqueous layers were washed with H2O (2×), dried over MgSO4 and concentrated under reduced pressure. Recrystallization (hexane/EtOAc) yields 3.01 g (83%) of a tan solid. 1H-NMR(CDCl3) 1.56 (s, 9H), 2.79 (s, 3H), 5.32 (s, 2H), 7.30-7.60 (m, 8H), 8.03 (d, 2H, J=8.0 Hz); mp=134-135° C.

Workup

  1. additionthe reaction was diluted
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with DCM
  4. washThe combined aqueous layers were washed with H2O (2×)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customRecrystallization (hexane/EtOAc)

Sources & evidence

ORD record
ord-bcbc3e68ff1f436e82aa1201b48c84de
Source dataset
uspto-grants-2000_03
Patent number
US06037340

Reaction notes

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